Reuben Feffer is a guy who's spent his entire life playing it safe. Polly Prince is irresistible as a free-spirit who lives for the thrill of the moment. When these two comically mismatched souls collide, Reuben's world is turned upside down, as he makes an uproarious attempt to change his life from middle-of-the-road to totally-out-there.
Peter Klaven is a successful real estate agent who, upon getting engaged to the woman of his dreams, Zooey, discovers, to his dismay and chagrin, that he has no male friend close enough to serve as his Best Man. Peter immediately sets out to rectify the situation, embarking on a series of bizarre and awkward "man-dates."
When a workaholic young executive, is left at the altar, she ends up on her Caribbean honeymoon cruise with the last person she ever expected: her estranged and equally workaholic father. The two depart as strangers, but over the course of a few hilarious adventures, a couple of umbrella-clad cocktails and a whole lot of soul-searching, they return with a renewed appreciation for family and life.
